Clickable Polyamine Derivatives as Chemical Probes for the Polyamine Transport System |
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| Authors: | Roeland Vanhoutte Jan Pascal Kahler Dr. Shaun Martin Sarah van Veen Prof. Dr. Steven H. L. Verhelst |
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| Affiliation: | 1. Laboratory of Chemical Biology, Department of Cellular and Molecular Medicine, KU Leuven, Leuven, Belgium;2. Laboratory of Cellular Transport Systems, Department of Cellular and Molecular Medicine, KU Leuven, Leuven, Belgium;3. Leibniz Institute for Analytical Sciences ISAS, Dortmund, Germany |
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| Abstract: | Polyamines are essential for cell growth and differentiation, but their trafficking by the polyamine transport system is not fully understood. Herein, the synthesis of several azido‐derivatized polyamines for easy conjugation by click chemistry is described. Attachment of a 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) dye gave fluorescent polyamine probes, which were tested in cell culture. The linear probe series showed superior cellular uptake compared with that of probes in which the dye was attached to a branch on one of the central amines. Interestingly, the linear probes accumulated rapidly in cancer cells (MCF‐7), but not in nontumorigenic cells (MCF‐10A). The fluorescent polyamine probes are therefore applicable to the study of polyamine trafficking, whereas the azido polyamines may be further utilized to transport cargo into cancer cells by exploiting the polyamine transport system. |
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| Keywords: | bioorganic chemistry click chemistry fluorescent probes imaging agents polyamines |
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